Propane sultone → 3-{[(1S)-1-(hydroxymethyl)-3-methylbutyl]amino}-1-propanesulfonic acid

To a solution of L-(+)-leucinol (5.0 g, 42.8 mmol) in THF (65 mL) was slowly added 1,3-propanesultone (4.85 g, 40.7 mmol in THF (10 mL)). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2×50 mL). The solid was dissolved in 50% water/EtOH (400 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid was suspended in acetone (150 mL), filtered and dried in the vacuum oven (50° C.), affording the title compound (6.11 g, 63%). 1H NMR (D2O, 500 MHz) δ ppm 3.77 (m, 1H), 3.59 (m, 1H), 3.23 (m, 1H), 3.13 (m, 2H), 2.90 (m, 2H), 2.02 (m, 2H), 1.53 (m, 2H), 1.35 (m, 1H), 0.81 (d, 3H, J=16.1 Hz). 13C (D2O, 125 MHz) δ ppm 58.72, 58.00, 48.17, 43.54, 35.96, 24.34, 22.53, 21.62, 20.89. [α]D=+16.6° (c=0.0022 in water), ES-MS 240 (M+1).

1. temperatureat reflux for 2 hours
2. filtrationThe solid was collected by filtration
3. washwashed with acetone (2×50 mL)
4. dissolutionThe solid was dissolved in 50% water/EtOH (400 mL)
5. additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
6. stirringThe suspension was stirred for 15 minutes before the resin
7. customwas removed by filtration
8. customThe filtrate was evaporated under reduced pressure
9. filtrationfiltered
10. customdried in the vacuum oven (50° C.)

ORD record

ord-4202d71426c04a34bdd48a12f4c7ddf4

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2